Kohei Torikai
Kyushu University, Japan
Title: 2-Naphthylmethoxymethyl: A Mildly Introducible and Oxidatively Removable Benzyloxymethyl-Type Protecting Group
Biography
Biography: Kohei Torikai
Abstract
Protective groups are still playing important roles in the synthesis of complex molecules, despite the recent negative campaign against using them that increase the E-factor and the number of steps. To expand the variety of protective groups, naphthylmethoxymethyl (NAPOM) was newly developed for the protection of hydroxy (including phenolic hydroxy and carboxy) and mercapto groups. The NAPOM group can be introduced in extremely mild conditions (NAPOMCl, 2,6-lutidine, rt) without concomitant acyl migration in a 1,2-diol system. Furthermore, selective removal of NAPOM in the presence of naphthylmethyl (NAP) and p-methoxybenzyl (PMB), and conversely, that of PMB in the presence of NAPOM, were realized. These results, as well as its easy handling and compatibility with various solvents, show that NAPOM is a novel and useful choice of protective groups.